3-Aminobenzoic Acid → Benzoic acid, 3-[[(methylamino)thioxomethyl]amino]-

HRID 611780Notes

Reaction equation

HRID 611780 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][N:12]=[C:13]=[S:14]>C(O)(=O)C>[CH3:11][NH:12][C:13](=[S:14])[NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 11167Methyl isothiocyanate

Product 1

HCID 893266Benzoic acid, 3-[[(methylamino)thioxomethyl]amino]-Yield 95.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 279.6 g of 3-amino-benzoic acid, 164.1 g of methyl isothiocyanate and 1000 g of 100% acetic acid is heated to 80-85° C. The temperature rises to 95-100° C. in the course of 20 minutes without further heating, and a clear solution from which the product slowly crystallizes out forms. The suspension is kept at 90-100° C. for 2 hours, subsequently cooled to 15-20° C. and filtered with suction and the material on the suction filter is washed with acetic acid. 404 g of the title compound result, purity: 99.5%, melting point: 190-91° C., decomposition. Yield: 95.7% of theory.

Workup

  1. customrises to 95-100° C. in the course of 20 minutes without further heating
  2. customa clear solution from which the product slowly crystallizes out forms
  3. temperaturesubsequently cooled to 15-20° C.
  4. filtrationfiltered with suction
  5. filtrationthe material on the suction filter
  6. washis washed with acetic acid

Sources & evidence

ORD record
ord-6921f5b474e34612b2c3232f7635b3d4
Source dataset
uspto-grants-1999_12
Patent number
US06002013

Reaction notes

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